The problem of figuring out "why" is that there are so MANY reasons people cross dress. Sometimes it is an activity associated with conditions like Transsexualism and for some reason, Homosexuality. More often in straight people we are looking at forms of fetishism, humiliation S/M, identity disassociation, escapism and stress relief, curiosity, or simply the "feel" of the fabric. And EACH motivation has it's own separate path. Before you can speculate WHY you started you have to honestly understand your motivation in the first place, and THEN determine how you got on the path. To further complicate things your reasons and motivations could change over time as you made more "fun" discoveries.